ES2938482T3 - Sulfato de condroitina reticulado, composición que contiene el mismo y agente de tratamiento para enfermedad ocular - Google Patents
Sulfato de condroitina reticulado, composición que contiene el mismo y agente de tratamiento para enfermedad ocular Download PDFInfo
- Publication number
- ES2938482T3 ES2938482T3 ES21150701T ES21150701T ES2938482T3 ES 2938482 T3 ES2938482 T3 ES 2938482T3 ES 21150701 T ES21150701 T ES 21150701T ES 21150701 T ES21150701 T ES 21150701T ES 2938482 T3 ES2938482 T3 ES 2938482T3
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- ES
- Spain
- Prior art keywords
- crosslinked
- group
- polyvalent amine
- agent
- chondroitin sulfate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 229920001287 Chondroitin sulfate Polymers 0.000 title claims description 24
- 229940059329 chondroitin sulfate Drugs 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 title abstract description 58
- 208000030533 eye disease Diseases 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 97
- 125000003277 amino group Chemical group 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims description 94
- 239000003795 chemical substances by application Substances 0.000 claims description 53
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 20
- 150000004985 diamines Chemical class 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- 230000009435 amidation Effects 0.000 claims description 8
- 238000007112 amidation reaction Methods 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 29
- 208000003556 Dry Eye Syndromes Diseases 0.000 abstract description 18
- 206010013774 Dry eye Diseases 0.000 abstract description 17
- 208000022873 Ocular disease Diseases 0.000 abstract description 10
- 210000003560 epithelium corneal Anatomy 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 description 47
- 238000004132 cross linking Methods 0.000 description 36
- 125000001931 aliphatic group Chemical group 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- 125000005842 heteroatom Chemical group 0.000 description 29
- 239000000047 product Substances 0.000 description 29
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- 208000035475 disorder Diseases 0.000 description 26
- 239000000843 powder Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000002953 phosphate buffered saline Substances 0.000 description 22
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 21
- 125000004429 atom Chemical group 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000003889 eye drop Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000002430 hydrocarbons Chemical class 0.000 description 15
- -1 alkaline earth metal salt Chemical class 0.000 description 14
- 230000035876 healing Effects 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 10
- 238000010186 staining Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004103 aminoalkyl group Chemical group 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 229940012356 eye drops Drugs 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 102000037716 Chondroitin-sulfate-ABC endolyases Human genes 0.000 description 7
- 108090000819 Chondroitin-sulfate-ABC endolyases Proteins 0.000 description 7
- 125000002015 acyclic group Chemical group 0.000 description 7
- 238000010171 animal model Methods 0.000 description 7
- 239000012620 biological material Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000002354 daily effect Effects 0.000 description 7
- 239000006196 drop Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000008215 water for injection Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 5
- 230000002159 abnormal effect Effects 0.000 description 5
- KXKPYJOVDUMHGS-OSRGNVMNSA-N chondroitin sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O1 KXKPYJOVDUMHGS-OSRGNVMNSA-N 0.000 description 5
- 210000004087 cornea Anatomy 0.000 description 5
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001133 acceleration Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 4
- 125000005263 alkylenediamine group Chemical group 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 229940097043 glucuronic acid Drugs 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229940063673 spermidine Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- FNEHAOQZWPHONV-UHFFFAOYSA-N 9h-carbazole;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C3=CC=CC=C3NC2=C1 FNEHAOQZWPHONV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- UYUXSRADSPPKRZ-UHFFFAOYSA-N D-glucuronic acid gamma-lactone Natural products O=CC(O)C1OC(=O)C(O)C1O UYUXSRADSPPKRZ-UHFFFAOYSA-N 0.000 description 3
- UYUXSRADSPPKRZ-SKNVOMKLSA-N D-glucurono-6,3-lactone Chemical compound O=C[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O UYUXSRADSPPKRZ-SKNVOMKLSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229950002441 glucurolactone Drugs 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
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- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- JONTXEXBTWSUKE-UHFFFAOYSA-N 2-(2-aminoethylsulfanyl)ethanamine Chemical compound NCCSCCN JONTXEXBTWSUKE-UHFFFAOYSA-N 0.000 description 2
- NIQFAJBKEHPUAM-UHFFFAOYSA-N 2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethanamine Chemical compound NCCOCCOCCOCCN NIQFAJBKEHPUAM-UHFFFAOYSA-N 0.000 description 2
- 229920002567 Chondroitin Polymers 0.000 description 2
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- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- DLGJWSVWTWEWBJ-HGGSSLSASA-N chondroitin Chemical compound CC(O)=N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@H](O)C=C(C(O)=O)O1 DLGJWSVWTWEWBJ-HGGSSLSASA-N 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 201000010099 disease Diseases 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
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- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000007970 homogeneous dispersion Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
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- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
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- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N o-phenylene-diaceto-nitrile Natural products N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 229940069265 ophthalmic ointment Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- SCHTXWZFMCQMBH-UHFFFAOYSA-N pentane-1,3,5-triamine Chemical compound NCCC(N)CCN SCHTXWZFMCQMBH-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- PZZICILSCNDOKK-UHFFFAOYSA-N propane-1,2,3-triamine Chemical compound NCC(N)CN PZZICILSCNDOKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 230000004488 tear evaporation Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/738—Cross-linked polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0069—Chondroitin-4-sulfate, i.e. chondroitin sulfate A; Dermatan sulfate, i.e. chondroitin sulfate B or beta-heparin; Chondroitin-6-sulfate, i.e. chondroitin sulfate C; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015007072 | 2015-01-16 | ||
| JP2015150976 | 2015-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2938482T3 true ES2938482T3 (es) | 2023-04-11 |
Family
ID=56405937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES21150701T Active ES2938482T3 (es) | 2015-01-16 | 2016-01-15 | Sulfato de condroitina reticulado, composición que contiene el mismo y agente de tratamiento para enfermedad ocular |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US10420796B2 (https=) |
| EP (2) | EP3831394B1 (https=) |
| JP (2) | JP6110037B2 (https=) |
| ES (1) | ES2938482T3 (https=) |
| WO (1) | WO2016114397A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019060696A1 (en) | 2017-09-25 | 2019-03-28 | Surface Pharmaceuticals, Inc. | OPTHALMIC PHARMACEUTICAL COMPOSITIONS AND METHODS FOR THE TREATMENT OF OCULAR SURFACE DISEASE |
| CA3124945A1 (en) | 2018-12-27 | 2020-07-02 | Surface Ophthalmics, Inc. | Ophthalmic pharmaceutical compositions and methods for treating ocular surface disease |
| BR112022018535A2 (pt) * | 2020-03-19 | 2022-11-29 | Glycologix Inc | Biomateriais de glicosaminoglicano sulfatado como miméticos de proteoglicanos |
| US12440510B2 (en) | 2021-05-10 | 2025-10-14 | Surface Ophthalmics, Inc. | Use of chondroitin sulfate for relieving ocular pain |
| US12310981B2 (en) | 2021-05-10 | 2025-05-27 | Surface Ophthalmics, Inc. | Use of chondroitin sulfate for relieving ocular pain |
| CN116687959B (zh) * | 2022-05-18 | 2024-10-22 | 朱小丰 | 一种硫酸软骨素生物多胺复合物、其制备方法及用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863907A (en) * | 1984-06-29 | 1989-09-05 | Seikagaku Kogyo Co., Ltd. | Crosslinked glycosaminoglycans and their use |
| US5527893A (en) | 1987-09-18 | 1996-06-18 | Genzyme Corporation | Water insoluble derivatives of polyanionic polysaccharides |
| RU2113221C1 (ru) | 1990-05-04 | 1998-06-20 | Ииссум Рисерч Дивелопмент Компани оф дзе Хебрю Юниверсити оф Иеруcалим | Фармацевтическая форма для введения лекарственного средства в ободочную кишку, способ введения лекарственного препарата и способ получения матриц для такой формы |
| IL98087A (en) | 1990-05-04 | 1996-11-14 | Perio Prod Ltd | Preparation for dispensing drugs in the colon |
| JP2855307B2 (ja) | 1992-02-05 | 1999-02-10 | 生化学工業株式会社 | 光反応性グリコサミノグリカン、架橋グリコサミノグリカン及びそれらの製造方法 |
| JPH07223966A (ja) | 1994-02-08 | 1995-08-22 | Seiko Epson Corp | 眼科用人工涙液 |
| JP3059092B2 (ja) | 1995-11-15 | 2000-07-04 | 田辺製薬株式会社 | ドライアイおよびドライアイを原因とする疾患の予防・治療剤 |
| IT1303738B1 (it) * | 1998-11-11 | 2001-02-23 | Aquisitio S P A | Processo di reticolazione di polisaccaridi carbossilati. |
| JP3903475B2 (ja) * | 1999-04-30 | 2007-04-11 | ニプロ株式会社 | 乾性角膜症治療剤 |
| CA2671572C (en) | 2006-12-04 | 2015-05-26 | Johns Hopkins University | Imidated biopolymer adhesive and hydrogel |
| EP3040117A1 (en) * | 2014-12-29 | 2016-07-06 | Galderma S.A. | Ether cross-linked chondroitin sulfate hydrogels and their use for soft tissue applications |
| WO2016107834A1 (en) * | 2014-12-29 | 2016-07-07 | Galderma S.A. | Carboxyl cross-linked chondroitin hydrogels and their use for soft tissue applications |
-
2016
- 2016-01-15 ES ES21150701T patent/ES2938482T3/es active Active
- 2016-01-15 EP EP21150701.7A patent/EP3831394B1/en active Active
- 2016-01-15 WO PCT/JP2016/051176 patent/WO2016114397A1/ja not_active Ceased
- 2016-01-15 EP EP16737468.5A patent/EP3246037A4/en not_active Withdrawn
- 2016-01-15 JP JP2016533212A patent/JP6110037B2/ja active Active
- 2016-01-15 US US15/543,748 patent/US10420796B2/en active Active
-
2017
- 2017-03-08 JP JP2017043621A patent/JP6715201B2/ja active Active
-
2019
- 2019-08-09 US US16/536,779 patent/US10716804B2/en active Active
-
2020
- 2020-06-09 US US16/896,823 patent/US11207345B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2016114397A1 (ja) | 2017-04-27 |
| WO2016114397A1 (ja) | 2016-07-21 |
| EP3831394B1 (en) | 2022-12-21 |
| US10420796B2 (en) | 2019-09-24 |
| EP3831394A1 (en) | 2021-06-09 |
| US20210052634A1 (en) | 2021-02-25 |
| JP6715201B2 (ja) | 2020-07-01 |
| US20190365796A1 (en) | 2019-12-05 |
| US20170368093A1 (en) | 2017-12-28 |
| JP6110037B2 (ja) | 2017-04-05 |
| EP3246037A4 (en) | 2018-07-11 |
| US11207345B2 (en) | 2021-12-28 |
| US10716804B2 (en) | 2020-07-21 |
| EP3246037A1 (en) | 2017-11-22 |
| JP2017125203A (ja) | 2017-07-20 |
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